AP1016A - Pyrrolidinyl and pyrrolinyl ethylamine compounds as opioid kappa receptor agonists. - Google Patents
Pyrrolidinyl and pyrrolinyl ethylamine compounds as opioid kappa receptor agonists. Download PDFInfo
- Publication number
- AP1016A AP1016A APAP/P/1997/001082A AP9701082A AP1016A AP 1016 A AP1016 A AP 1016A AP 9701082 A AP9701082 A AP 9701082A AP 1016 A AP1016 A AP 1016A
- Authority
- AP
- ARIPO
- Prior art keywords
- methylamino
- phenylethyl
- hydroxypyrrolidin
- alkyl
- phenyl
- Prior art date
Links
- 102000048260 kappa Opioid Receptors Human genes 0.000 title description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 title description 4
- 108020001588 κ-opioid receptors Proteins 0.000 title description 4
- KRRLFZPRZPZNPW-UHFFFAOYSA-N n-ethyl-2,3-dihydropyrrol-1-amine Chemical class CCNN1CCC=C1 KRRLFZPRZPZNPW-UHFFFAOYSA-N 0.000 title description 3
- 239000000018 receptor agonist Substances 0.000 title description 3
- 229940044601 receptor agonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 13
- 239000001257 hydrogen Substances 0.000 abstract description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract description 11
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 239000000556 agonist Substances 0.000 abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 abstract description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- 150000003235 pyrrolidines Chemical class 0.000 abstract description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 description 25
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- -1 PYRROLIDINYL Chemical class 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 6
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000000730 antalgic agent Substances 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000002632 kappa opiate receptor agonist Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 102000003840 Opioid Receptors Human genes 0.000 description 2
- 108090000137 Opioid Receptors Proteins 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 239000002756 mu opiate receptor agonist Substances 0.000 description 2
- 239000004090 neuroprotective agent Substances 0.000 description 2
- 239000000014 opioid analgesic Substances 0.000 description 2
- 229940005483 opioid analgesics Drugs 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000005543 phthalimide group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- XXZDIDFBKZKGQB-RYUDHWBXSA-N (1r)-2-[(3s)-3-fluoropyrrolidin-1-yl]-1-phenylethanol Chemical compound C([C@H](O)C=1C=CC=CC=1)N1CC[C@H](F)C1 XXZDIDFBKZKGQB-RYUDHWBXSA-N 0.000 description 1
- XXZDIDFBKZKGQB-VXGBXAGGSA-N (1s)-2-[(3r)-3-fluoropyrrolidin-1-yl]-1-phenylethanol Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1CC[C@@H](F)C1 XXZDIDFBKZKGQB-VXGBXAGGSA-N 0.000 description 1
- XXZDIDFBKZKGQB-NWDGAFQWSA-N (1s)-2-[(3s)-3-fluoropyrrolidin-1-yl]-1-phenylethanol Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1CC[C@H](F)C1 XXZDIDFBKZKGQB-NWDGAFQWSA-N 0.000 description 1
- AOKXUMARJFHZNA-LBPRGKRZSA-N (2r)-2-(2,5-dihydropyrrol-1-yl)-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC=CC1 AOKXUMARJFHZNA-LBPRGKRZSA-N 0.000 description 1
- TTZHTKJTUXXCEX-NEPJUHHUSA-N (2r)-2-[(3r)-3-fluoropyrrolidin-1-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC[C@@H](F)C1 TTZHTKJTUXXCEX-NEPJUHHUSA-N 0.000 description 1
- NWZKEQHPACLAPF-RYUDHWBXSA-N (2r)-2-[(3s)-3-chloropyrrolidin-1-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC[C@H](Cl)C1 NWZKEQHPACLAPF-RYUDHWBXSA-N 0.000 description 1
- TTZHTKJTUXXCEX-RYUDHWBXSA-N (2r)-2-[(3s)-3-fluoropyrrolidin-1-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)CC[C@H](F)C1 TTZHTKJTUXXCEX-RYUDHWBXSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- FVPPPNWXMSRIOO-AVVPKOCDSA-N 2-[3-[[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-methylamino]pyrrolidin-1-yl]benzamide Chemical compound C([C@@H](N(C)C1CN(CC1)C=1C(=CC=CC=1)C(N)=O)C=1C=CC=CC=1)N1CC[C@H](O)C1 FVPPPNWXMSRIOO-AVVPKOCDSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- CPGURIUARAKJJE-JIOHBXSKSA-N OC[C@@H](N1CC[C@H](F)C1)c1ccccc1.O[C@H](CN1CC[C@H](Cl)C1)c1ccccc1 Chemical compound OC[C@@H](N1CC[C@H](F)C1)c1ccccc1.O[C@H](CN1CC[C@H](Cl)C1)c1ccccc1 CPGURIUARAKJJE-JIOHBXSKSA-N 0.000 description 1
- 102000001490 Opioid Peptides Human genes 0.000 description 1
- 108070000021 Opioid peptides receptors Proteins 0.000 description 1
- 206010053615 Thermal burn Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- JHLHNYVMZCADTC-LOSJGSFVSA-N asimadoline Chemical compound C([C@@H](N(C)C(=O)C(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 JHLHNYVMZCADTC-LOSJGSFVSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IBPCT/IB96/00957 | 1996-09-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9701082A0 AP9701082A0 (en) | 1997-10-31 |
| AP1016A true AP1016A (en) | 2001-10-08 |
Family
ID=11004480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/001082A AP1016A (en) | 1996-09-18 | 1997-09-11 | Pyrrolidinyl and pyrrolinyl ethylamine compounds as opioid kappa receptor agonists. |
Country Status (38)
| Country | Link |
|---|---|
| US (7) | US6201007B1 (fr) |
| EP (1) | EP0934264B1 (fr) |
| JP (2) | JP3195368B2 (fr) |
| KR (1) | KR100339666B1 (fr) |
| CN (1) | CN1237962A (fr) |
| AP (1) | AP1016A (fr) |
| AR (1) | AR008168A1 (fr) |
| AT (1) | ATE249433T1 (fr) |
| AU (1) | AU719895B2 (fr) |
| BG (1) | BG64194B1 (fr) |
| BR (1) | BR9711506A (fr) |
| CA (1) | CA2266006C (fr) |
| CO (1) | CO4920224A1 (fr) |
| DE (1) | DE69724805T2 (fr) |
| DK (1) | DK0934264T3 (fr) |
| DZ (1) | DZ2309A1 (fr) |
| EA (1) | EA001341B1 (fr) |
| ES (1) | ES2205248T3 (fr) |
| HR (1) | HRP970509A2 (fr) |
| ID (1) | ID19611A (fr) |
| IL (3) | IL128959A0 (fr) |
| IS (1) | IS4992A (fr) |
| MA (1) | MA26441A1 (fr) |
| NO (1) | NO313550B1 (fr) |
| NZ (1) | NZ334439A (fr) |
| OA (1) | OA10996A (fr) |
| PA (1) | PA8437201A1 (fr) |
| PE (1) | PE109998A1 (fr) |
| PL (1) | PL332546A1 (fr) |
| PT (1) | PT934264E (fr) |
| SK (1) | SK32799A3 (fr) |
| TN (2) | TNSN97092A1 (fr) |
| TR (1) | TR199900590T2 (fr) |
| TW (1) | TW432047B (fr) |
| UA (1) | UA60310C2 (fr) |
| WO (1) | WO1998012177A1 (fr) |
| YU (1) | YU13899A (fr) |
| ZA (1) | ZA978358B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6420391B1 (en) * | 1998-04-01 | 2002-07-16 | Ono Pharmaceutical Co., Ltd. | Fused thiophone derivatives and drugs containing the same as the active ingredient |
| IL130429A0 (en) * | 1998-08-24 | 2000-06-01 | Pfizer Prod Inc | Process for preparing pyrrolidinyl hydroxamic acid compounds |
| WO2002088082A2 (fr) * | 2001-04-30 | 2002-11-07 | Pfizer Products Inc. | Procede de preparation de composes d'ethylamine d'hydroxypyrrolidinyle utilises comme agonistes de kappa |
| WO2003072544A1 (fr) * | 2002-02-28 | 2003-09-04 | Pfizer Products Inc. | Sels de benzoate monohydrates et anhydres cristallises de (2's,3s)-3-hydroxy-n-{2-[n-methyl-n-4-(n-propylamino-carbonyl)phenyl]amino-2-phenyl}-ethylpyrrolidine |
| AU2003269399A1 (en) * | 2002-11-01 | 2004-05-25 | Pfizer Products Inc. | Process for the preparation of pyrrolidinyl ethylamine compounds via a copper-mediated aryl amination |
| CN1972914A (zh) * | 2004-03-31 | 2007-05-30 | 詹森药业有限公司 | 作为组胺h3受体配合体的非咪唑杂环化合物 |
| US7746514B2 (en) * | 2004-04-14 | 2010-06-29 | Hung-Yi Hsu | Scanner and exposure control method thereof |
| RU2303448C2 (ru) * | 2005-04-28 | 2007-07-27 | Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУ ВПО ПГФА Росздрава) | 3-гидрокси-5-(3-нитрофенил)-4-(4-хлорбензоил)-1-(2-диэтиламиноэтил)-3-пирролин-2-она гидрохлорид, проявляющий противовоспалительную активность |
| US20080058312A1 (en) * | 2006-01-11 | 2008-03-06 | Angion Biomedica Corporation | Modulators of hepatocyte growth factor/c-Met activity |
| EA015555B1 (ru) | 2006-05-30 | 2011-08-30 | Янссен Фармацевтика Н.В. | Замещенные пиридиламидные соединения в качестве модуляторов гистаминового h-рецептора |
| JP2009542706A (ja) * | 2006-06-29 | 2009-12-03 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ヒスタミンｈ３受容体の置換ベンズアミドモジュレーター |
| KR101546712B1 (ko) | 2007-11-20 | 2015-08-24 | 얀센 파마슈티카 엔.브이. | 히스타민 ｈ3 수용체의 조절제로서 사이클로알킬옥시- 및 헤테로사이클로알킬옥시피리딘 화합물 |
| RU2413512C1 (ru) * | 2009-07-29 | 2011-03-10 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | Средство, обладающее каппа-опиоидной агонистической активностью |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0483580A2 (fr) * | 1990-11-02 | 1992-05-06 | MERCK PATENT GmbH | 1-(2-Aryléthyl)-pyrrolidines |
| WO1994018165A1 (fr) * | 1993-02-12 | 1994-08-18 | Pfizer Inc. | Composes de sulfonamide utilises comme agonistes des recepteurs k d'opioides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8801304D0 (en) | 1988-01-21 | 1988-02-17 | Ici Plc | Diamine compounds |
| US5232978A (en) * | 1988-12-23 | 1993-08-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 1-(2-arylethyl)-pyrrolidines |
| DE3935371A1 (de) * | 1988-12-23 | 1990-07-05 | Merck Patent Gmbh | Stickstoffhaltige ringverbindungen |
| IL117440A0 (en) | 1995-03-31 | 1996-07-23 | Pfizer | Pyrrolidinyl hydroxamic acid compounds and their production process |
-
1997
- 1997-05-27 TN TNTNSN97092A patent/TNSN97092A1/fr unknown
- 1997-08-20 TW TW086111948A patent/TW432047B/zh active
- 1997-08-21 YU YU13899A patent/YU13899A/sh unknown
- 1997-08-21 UA UA99031459A patent/UA60310C2/uk unknown
- 1997-08-21 EA EA199900209A patent/EA001341B1/ru not_active IP Right Cessation
- 1997-08-21 DK DK97934676T patent/DK0934264T3/da active
- 1997-08-21 CN CN97199817A patent/CN1237962A/zh active Pending
- 1997-08-21 US US09/254,805 patent/US6201007B1/en not_active Expired - Fee Related
- 1997-08-21 NZ NZ334439A patent/NZ334439A/xx unknown
- 1997-08-21 EP EP97934676A patent/EP0934264B1/fr not_active Expired - Lifetime
- 1997-08-21 PL PL97332546A patent/PL332546A1/xx unknown
- 1997-08-21 TR TR1999/00590T patent/TR199900590T2/xx unknown
- 1997-08-21 IL IL12895997A patent/IL128959A0/xx unknown
- 1997-08-21 SK SK327-99A patent/SK32799A3/sk unknown
- 1997-08-21 BR BR9711506A patent/BR9711506A/pt not_active Application Discontinuation
- 1997-08-21 DE DE69724805T patent/DE69724805T2/de not_active Expired - Fee Related
- 1997-08-21 IL IL14736797A patent/IL147367A0/xx unknown
- 1997-08-21 PT PT97934676T patent/PT934264E/pt unknown
- 1997-08-21 JP JP51443398A patent/JP3195368B2/ja not_active Expired - Fee Related
- 1997-08-21 ES ES97934676T patent/ES2205248T3/es not_active Expired - Lifetime
- 1997-08-21 WO PCT/IB1997/001021 patent/WO1998012177A1/fr not_active Application Discontinuation
- 1997-08-21 KR KR1019997002287A patent/KR100339666B1/ko not_active Expired - Fee Related
- 1997-08-21 AT AT97934676T patent/ATE249433T1/de not_active IP Right Cessation
- 1997-08-21 AU AU37812/97A patent/AU719895B2/en not_active Ceased
- 1997-08-21 IL IL14736897A patent/IL147368A0/xx unknown
- 1997-08-21 CA CA002266006A patent/CA2266006C/fr not_active Expired - Fee Related
- 1997-08-29 PA PA19978437201A patent/PA8437201A1/es unknown
- 1997-09-04 AR ARP970104054A patent/AR008168A1/es not_active Application Discontinuation
- 1997-09-11 AP APAP/P/1997/001082A patent/AP1016A/en active
- 1997-09-15 MA MA24796A patent/MA26441A1/fr unknown
- 1997-09-16 TN TNTNSN97156A patent/TNSN97156A1/fr unknown
- 1997-09-16 ID IDP973203A patent/ID19611A/id unknown
- 1997-09-17 CO CO97054286A patent/CO4920224A1/es unknown
- 1997-09-17 ZA ZA978358A patent/ZA978358B/xx unknown
- 1997-09-17 DZ DZ970159A patent/DZ2309A1/fr active
- 1997-09-18 PE PE1997000834A patent/PE109998A1/es not_active Application Discontinuation
- 1997-09-18 HR HRPCT/IB96/00957A patent/HRP970509A2/hr not_active Application Discontinuation
-
1999
- 1999-03-05 IS IS4992A patent/IS4992A/is unknown
- 1999-03-11 BG BG103239A patent/BG64194B1/bg unknown
- 1999-03-12 OA OA9900057A patent/OA10996A/en unknown
- 1999-03-17 NO NO19991294A patent/NO313550B1/no unknown
-
2001
- 2001-01-26 US US09/770,512 patent/US6303602B1/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,514 patent/US6294569B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,513 patent/US6313302B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/770,515 patent/US6310061B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/771,029 patent/US6307061B2/en not_active Expired - Fee Related
- 2001-01-26 US US09/771,030 patent/US6294557B1/en not_active Expired - Fee Related
- 2001-03-28 JP JP2001092342A patent/JP2001316344A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0483580A2 (fr) * | 1990-11-02 | 1992-05-06 | MERCK PATENT GmbH | 1-(2-Aryléthyl)-pyrrolidines |
| WO1994018165A1 (fr) * | 1993-02-12 | 1994-08-18 | Pfizer Inc. | Composes de sulfonamide utilises comme agonistes des recepteurs k d'opioides |
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